Water → HCID 66686005, compound

HRID 1697315Notes

Reaction equation

HRID 1697315 reaction equation
CS(Cl)(=O)=O.[CH:6]1([NH:9][C:10](=[O:39])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C@@H:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH2:35][CH2:36]O)[CH2:26][CH3:27])[C:19]3=[O:38])[CH:12]=2)[CH2:8][CH2:7]1.[CH2:40]([N:42](CC)[CH2:43][CH3:44])[CH3:41].O>ClCCl>[CH:6]1([NH:9][C:10](=[O:39])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C@@H:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH2:35][CH2:36][N:42]4[CH2:43][CH2:44][CH2:41][CH2:40]4)[CH2:26][CH3:27])[C:19]3=[O:38])[CH:12]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66690017HCID 66690017, compound

Product 1

HCID 66686005HCID 66686005, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.21 mL) was added to a stirred solution of N-cyclopropyl-3-[3-[[(1R)-1-[2-(2-hydroxyethoxy)phenyl]propyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzamide (410 mg) and triethylamine (0.5 mL) in dichloromethane (10 mL) at 0° C. The mixture was stirred for 1 h at 0° C. and 1 h at room temperature. Water was added and the organic phase was separated, (Na2SO4), filtered and concentrated in vacuo. The residue was treated with dichloromethane (10 mL) and pyrrolidine (0.73 mL) and the mixture was stirred at room temperature for 24 h. The mixture was concentrated in vacu. Purification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent) afforded the title compound as a solid (147 mg).

Workup

  1. customthe organic phase was separated, (Na2SO4),
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. additionThe residue was treated with dichloromethane (10 mL) and pyrrolidine (0.73 mL)
  5. stirringthe mixture was stirred at room temperature for 24 h
  6. concentrationThe mixture was concentrated in vacu
  7. customPurification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent)

Sources & evidence

ORD record
ord-d585467733a94b819f9fdd6c2dd683d2
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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